Live data — refreshed 5:58 PM CDT
Apartments in Uptown Under $2,000
85 apartments available in Uptown under $2,000. Median rent $1,750. Live prices and availability.
About Uptown: Historic entertainment district on the north lakefront — old jazz-era theaters (Aragon, Riviera, Uptown), a long stretch of lakefront, and a mix of vintage apartment buildings and new construction. Improving steadily over the last decade.
$1,750
Median rent
$1,234
Cheapest
Available now
$1,234
Studio · 333sf
The Winnie #320
Uptown
$1,313
1BR · 471sf
The Winnie #219
Uptown
$1,331
Studio · 317sf
The Lawrence House #1026
Uptown
$1,331
Studio · 298sf
The Lawrence House #1104
Uptown
$1,349
Studio · 300sf
The Lawrence House #405
Uptown
$1,420
Studio
Reside at 849 #55D3
Uptown
$1,433
Studio · 319sf
The Lawrence House #1124
Uptown
$1,487
Studio
Reside at 823 #0207
Uptown
$1,491
Studio · 303sf
The Lawrence House #1021
Uptown
$1,491
Studio · 303sf
The Lawrence House #421
Uptown
$1,511
Studio · 305sf
The Lawrence House #1014
Uptown
$1,511
Studio · 289sf
The Lawrence House #712
Uptown
$1,524
Studio · 448sf
The Lawrence House #416
Uptown
$1,535
Studio
Reside on Clarendon #0508
Uptown
$1,542
Studio · 236sf
The Lawrence House #1224
Uptown
$1,550
Studio · 362sf
The June #A1
Uptown
$1,553
Studio
Reside at 823 #0306
Uptown
$1,554
Studio · 300sf
The Lawrence House #1207
Uptown
$1,570
Studio
Reside at 823 #0204
Uptown
$1,583
Studio
The Covington #0102
Uptown
$1,595
Studio · 359sf
The Winnie #421
Uptown
$1,600
Studio
Buena Terrace #0413
Uptown
$1,610
Studio · 410sf
The Winnie #310
Uptown
$1,635
1BR
Buena Terrace #0106
Uptown
$1,675
Studio · 410sf
The Winnie #210
Uptown
$1,695
Studio · 481sf
The Winnie #228
Uptown
$1,695
Studio · 408sf
The Sally #A303
Uptown
$1,695
Studio · 406sf
The Draper #630
Uptown
$1,695
Studio · 391sf
The Draper #639
Uptown
$1,710
Studio · 412sf
The Draper #610
Uptown
Top buildings for this search
- The Lawrence House$1,331–$1,981
- Platform 4611$1,750–$1,985
- The Winnie$1,234–$1,895
- Reside on Clarendon$1,535–$1,972
- The Draper$1,695–$1,780
- The Covington$1,583–$1,981
- The Teller House$1,715–$1,975
- Buena Terrace$1,600–$1,792
Frequently asked
What's the cheapest in Uptown under $2,000 right now?
The Winnie #320 at $1,234/month, 333 square feet. Located at 4750 N Winthrop Ave.
How many apartments are available in Uptown under $2,000?
Apartments are currently listed in Uptown under $2,000. Median rent is $1,750.
Which buildings in Uptown offer apartments?
Top buildings by current inventory: The Lawrence House, Platform 4611, The Winnie, Reside on Clarendon, The Draper.
Is $2,000 a realistic budget for in Uptown?
Yes. The median rent at this size in Uptown is $1,750, so a $2,000 ceiling sits $250 above the median and leaves room to choose.
Compare Uptown to nearby neighborhoods
More in Uptown
Updated September 20, 2026 at 5:58 PM CDT. No paid placement.